FR2375161A1 - PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S) - Google Patents

PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S)

Info

Publication number
FR2375161A1
FR2375161A1 FR7612094A FR7612094A FR2375161A1 FR 2375161 A1 FR2375161 A1 FR 2375161A1 FR 7612094 A FR7612094 A FR 7612094A FR 7612094 A FR7612094 A FR 7612094A FR 2375161 A1 FR2375161 A1 FR 2375161A1
Authority
FR
France
Prior art keywords
acid ester
chiral acid
cyane
secondary alcohol
optically active
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7612094A
Other languages
French (fr)
Other versions
FR2375161B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9172256&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FR2375161(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7612094A priority Critical patent/FR2375161A1/en
Priority to NO771244A priority patent/NO149104C/en
Priority to OA56142A priority patent/OA05636A/en
Priority to SE7704518A priority patent/SE446629B/en
Priority to YU1047/77A priority patent/YU40297B/en
Priority to CA276,725A priority patent/CA1130311A/en
Priority to AR267315A priority patent/AR228557A1/en
Priority to DE2718039A priority patent/DE2718039C2/en
Priority to PL1977213280A priority patent/PL113207B1/en
Priority to SU772481551A priority patent/SU990082A3/en
Priority to GB16866/77A priority patent/GB1582595A/en
Priority to HU77RO923A priority patent/HU181942B/en
Priority to BE176937A priority patent/BE853867A/en
Priority to PT66468A priority patent/PT66468B/en
Priority to CH506077A priority patent/CH620889A5/fr
Priority to BR7702576A priority patent/BR7702576A/en
Priority to MX775658U priority patent/MX5299E/en
Priority to LU77183A priority patent/LU77183A1/xx
Priority to DD7700198553A priority patent/DD130929A5/en
Priority to DK177077A priority patent/DK171573B1/en
Priority to IT49095/77A priority patent/IT1073208B/en
Priority to ES458112A priority patent/ES458112A1/en
Priority to US05/789,842 priority patent/US4136195A/en
Priority to US05/789,774 priority patent/US4133826A/en
Priority to PL1977197553A priority patent/PL117200B1/en
Priority to GB16867/77A priority patent/GB1582596A/en
Priority to JP4729977A priority patent/JPS52131559A/en
Priority to GR53282A priority patent/GR63104B/en
Priority to JP4729877A priority patent/JPS52148040A/en
Priority to AT289677A priority patent/AT360970B/en
Priority to IE831/77A priority patent/IE45496B1/en
Priority to TR19049A priority patent/TR19049A/en
Priority to NLAANVRAGE7704521,A priority patent/NL180934C/en
Priority to ZA00772474A priority patent/ZA772474B/en
Priority to AT0929178A priority patent/AT364675B/en
Priority to CS772711A priority patent/CS214851B2/en
Priority to NZ183938A priority patent/NZ183938A/en
Priority to AU24595/77A priority patent/AU512155B2/en
Priority to IL51958A priority patent/IL51958A/en
Priority to FR7717014A priority patent/FR2421876A1/en
Publication of FR2375161A1 publication Critical patent/FR2375161A1/en
Application granted granted Critical
Publication of FR2375161B1 publication Critical patent/FR2375161B1/fr
Priority to GT197957492A priority patent/GT197957492A/en
Priority to AT125880A priority patent/AT366028B/en
Priority to CS81436A priority patent/CS214852B2/en
Priority to SE8204715A priority patent/SE449359B/en
Priority to SG232/84A priority patent/SG23284G/en
Priority to SG231/84A priority patent/SG23184G/en
Priority to HK518/84A priority patent/HK51884A/en
Priority to HK519/84A priority patent/HK51984A/en
Priority to NLAANVRAGE8502001,A priority patent/NL188676C/en
Priority to MY509/85A priority patent/MY8500509A/en
Priority to DK317589A priority patent/DK170732B1/en
Priority to HRP-1047/77A priority patent/HRP931394B1/en
Priority to MD94-0277A priority patent/MD245C2/en
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)

Abstract

L'invention a pour objet un procédé de transformation d'un ester d'acide chiral A d'alcool secondaire alpha -cyané B optiquement actif de structure R en ester d'acide chiral A d'alcool secondaire alpha -cyané B optiquement actif de structure S caractérisé en ce que l'on soumet l'ester d'acide chiral A d'alcool B optiquement actif de structure R à l'action d'un agent basique choisi dans le groupe constitué par l'ammoniaque, les amines secondaires, les amines tertiaires et les bases fortes qui, elles, sont utilisées en quantité catalytique, au sein d'un solvant ou d'un mélange de solvants dans lequel l'ester d'acide chiral A d'alcool B de structure S est insoluble, et l'ester d'acide chiral A d'alcool B de structure R est soluble, puis isole du milieu réactionnel, l'ester d'acide chiral A d'alcool B de structure S ainsi insolubilisé.The subject of the invention is a process for converting a chiral acid ester A of optically active alpha-cyan secondary alcohol B of structure R into a chiral acid ester A of optically active alpha-cyanated secondary alcohol B of structure S, characterized in that the optically active alcohol B chiral acid ester A of structure R is subjected to the action of a basic agent chosen from the group consisting of ammonia and secondary amines, tertiary amines and strong bases which, for their part, are used in a catalytic amount, in a solvent or a mixture of solvents in which the chiral acid ester A of alcohol B of structure S is insoluble, and the chiral acid ester A of alcohol B of structure R is soluble, then isolated from the reaction medium, the chiral acid ester A of alcohol B of structure S thus insolubilized.

FR7612094A 1976-04-23 1976-04-23 PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S) Granted FR2375161A1 (en)

Priority Applications (53)

Application Number Priority Date Filing Date Title
FR7612094A FR2375161A1 (en) 1976-04-23 1976-04-23 PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S)
NO771244A NO149104C (en) 1976-04-23 1977-04-06 PROCEDURE FOR PREPARING ESTERS OF 2,2-DIMETHYL-3- (2`, 2`-SUBSTITUTED-VINYL) -CYCLOPROPAN-CARBOXYLIC ACID AND ALFA-CYANO-3-PHENOXYVENZYL ALCOHOL (S)
OA56142A OA05636A (en) 1976-04-23 1977-04-15 Process for converting an optically active secondary alcohol-cyanated chiral acid ester of structure (R) into a secondary alcohol-cyaninated chiral acid ester of structure (S), insecticidal products and compositions.
SE7704518A SE446629B (en) 1976-04-23 1977-04-20 METHOD OF CONVERTING AN OPTICALLY ACTIVE ESTER OF A CIRAL ACID AND ONE SECOND ALFA CYANAL ALCOHOL WITH THE STRUCTURE (S) TO AN ESTER OF A CIRAL ACID AND ONE SECOND ALFA CYANAL ALCOHOL WITH THE STRUCTURE (S)
YU1047/77A YU40297B (en) 1976-04-23 1977-04-21 Process for transforming esters of cis-or trans-2,2-dimethyl-3r-(2,2-dihalovinyl)-cyclopropane-1r-carboxylic acid
CA276,725A CA1130311A (en) 1976-04-23 1977-04-21 PROCESS FOR THE TRANSFORMATION OF AN ESTER OF CHIRAL ACID AND OF AN OPTICALLY ACTIVE .alpha.-CYANATED SECONDARY ALCOHOL OF (R) STRUCTURE TO AN ESTER OF CHIRAL ACID AND OF AN .ALPHA.-CYANATED SECONDARY ALCOHOL OF (S) STRUCTURE
AR267315A AR228557A1 (en) 1976-04-23 1977-04-22 PROCESS FOR THE TRANSFORMATION OF AN OPTICALLY ACTIVE ALPHA-CYAN SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO AN ALPHA-CYAN SECONDARY ALCOHOL ESTER OF STRUCTURE (S) PRODUCTS AND COMPOSITIONS
DE2718039A DE2718039C2 (en) 1976-04-23 1977-04-22 A process for converting an ester of an optically active cyclopropanecarboxylic acid and an optically active alcohol of structure (R) into an ester of the chiral acid of the optically active alcohol of structure (S), (S) -α-cyano-3-phenoxybenzyl-2, 2-dimethyl-3R- (2,2-dichlorovinyl) -cyclopropane-1R-carboxylate and insecticidal agents containing the same
PL1977213280A PL113207B1 (en) 1976-04-23 1977-04-22 Insecticide
SU772481551A SU990082A3 (en) 1976-04-23 1977-04-22 Process for preparing (s)-alpha-cyano-3-phenoxybenzene ester of cis- or trans-2,2-dimethyl-3r-(2,2-dihalovinyl)-cyclopropane-1-r-carboxylic acid
GB16866/77A GB1582595A (en) 1976-04-23 1977-04-22 Chiral acid esters
HU77RO923A HU181942B (en) 1976-04-23 1977-04-22 Insecticide compositions containing esters of bracket-s-bracket closed-alpha-cyano-sec-alcohols with kyral acids and process for producing the active agents with transforming the ester containing bracket-r-bracket closed isomere of the alcohol
BE176937A BE853867A (en) 1976-04-23 1977-04-22 PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE SECONDARY ALPHA-CYANE CHIRAL ACID ESTER OF STRUCTURE (R) INTO ESTER OF CHIRAL ACID OF SECONDARY ALPHA-CYANE STRUCTURE (S) ALPHA-CYANE
PT66468A PT66468B (en) 1976-04-23 1977-04-22 PROCESS FOR PROCESSING AN OPTICALLY ACTIVE ALPHA-CYANE SECONDARY ALCOHOL CHIRAL ESTER OF CHIRAL ALPHA-CYANE SECONDARY ALCOHOL ESTER STRUCTURE (R) OF STRUCTURE (S)
CH506077A CH620889A5 (en) 1976-04-23 1977-04-22
BR7702576A BR7702576A (en) 1976-04-23 1977-04-22 PROCESS OF TRANSFORMATION OF AN OPTICALLY ACTIVE ALCOHOL CHEMICAL ACID ESTER OF STRUCTURE (R) IN STRUCTURAL ALCOHOL CHIRALIC ACID (S) AND COMPOSITES
MX775658U MX5299E (en) 1976-04-23 1977-04-22 PROCEDURE FOR TRANSFORMING AN OPTICALLY ACTIVE STRUCTURE (R) OR RACEMIC (R, S) SECONDARY ALPHA-CYAN SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE ALPHA-CYANATE SECONDARY ALCOHOL ESTER (S)
LU77183A LU77183A1 (en) 1976-04-23 1977-04-22
DD7700198553A DD130929A5 (en) 1976-04-23 1977-04-22 PROCESS FOR CONVERTING AN OPTICALLY ACTIVE ALPHA-ZYANO-SEK-ALCOHOL CHALINE ACID ESTERS
DK177077A DK171573B1 (en) 1976-04-23 1977-04-22 Process for converting a chiral ester between a dihalogenated cyclopropane carboxylic acid with two asymmetric carbon atoms in the ring and an optically active alpha cyanated secondary alcohol of R structure or a racemic alcohol of R, S structure or the chiral ester is a mixture of esters of alcohol of R structure and alcohol of S structure to ester between said acid and alcohol of S structure
IT49095/77A IT1073208B (en) 1976-04-23 1977-04-22 PROCEDURE FOR THE TRANSFORMATION OF A CHIRAL ACID ESTER WITH SECONDARY ALPHA-CYANATE OPTICALLY ACTIVE ALCOHOL OF STRUCTURE R IN AND CHIRAL ACID ESTER WITH A SECONDARY ALPHA-CYANATE STRUCTURE ALCOHOL S PRODUCT OBTAINED AND INSECTICON COMPOSITION AS A CONTINENT
ES458112A ES458112A1 (en) 1976-04-23 1977-04-22 Novel inversion process
US05/789,842 US4136195A (en) 1976-04-23 1977-04-22 Insecticidal cyclopropane carboxylates
US05/789,774 US4133826A (en) 1976-04-23 1977-04-22 Novel inversion process
PL1977197553A PL117200B1 (en) 1976-04-23 1977-04-22 Method of transformatiom of ester of chirallic acid with optically active,secondary alpha-cyano alcohol of /r/ configuration,into ester of chirallic acid with secondary alpha-cyano alcohol of/s/configurationski aktivnym vtorichnym-cianovym spirtom s konfiguraciejj/r/w efir khiralevojj kisloty so vtorichnym-cianovym siirtom s konfiguraciejj/s/
GB16867/77A GB1582596A (en) 1976-04-23 1977-04-22 Cyclopropane carboxylic esters
JP4729977A JPS52131559A (en) 1976-04-23 1977-04-23 New cyclopropane carboxylic acid ester and insecticide compositions
GR53282A GR63104B (en) 1976-04-23 1977-04-23 Process for the transformation of an ester of an optically active acid with a secondary,a-cyanated optically active alcohol of r structure to an ester of an optically active acid with a secondary a cyanated,optically active alcohol of s structure,products and insecticidal compositions
JP4729877A JPS52148040A (en) 1976-04-23 1977-04-23 Method of converting chiralic acid of optically active alphaacyano secondary alcohol with *r* configuration to acid of alphaacyano secondary alcohol and pesticidal composition
AT289677A AT360970B (en) 1976-04-23 1977-04-25 METHOD FOR PRODUCING A 2,2-DIMETHYL-3R - (2'-SUBSTITUTED VINYL) -CYCLOPROPANCARBONIC ACID ESTER WITH THE (S) -ALPHA-CYANO-3-PHENOXY-BENZYL ALCOHOL
IE831/77A IE45496B1 (en) 1976-04-23 1977-04-25 Chiral acid esters
TR19049A TR19049A (en) 1976-04-23 1977-04-25 THE ESTER OF THE ACID SIRAL OF THE ALPHA-CYANE ALCOHOL SECONDER IN THE OPTICALLY ACTIVE (R) STRUEKTUERINE (S) IN THE STRUECTUER OF THE ALPHA-CYANAL ALCOHOL SECONDARY
NLAANVRAGE7704521,A NL180934C (en) 1976-04-23 1977-04-25 PROCESS FOR THE PREPARATION OF AN ESTER OF A CHIRAL 3 (SUBSTITUTED VINYL) CYCLOPROPANIC CARBONIC ACID WITH TWO CARBON ATOMS OF THE RING ASYMMETRIC CARBON ATOMS WITH AN OPTICALLY ACTIVE ALPHA-CYANOHOLENOUSPHOLENOUSPHOLENOUS-3-CYANO -PHENOUS-PHENOHOLENOUS-PHENOHOLENOUS.
ZA00772474A ZA772474B (en) 1976-04-23 1977-04-25 Process for converting a chiral acid ester of an optically-active a-cyano secondary alcohol of structure(r)into a chiral acid ester of a-cyano secondary alcohol of structure(s),products and insecticidal compositions
AT0929178A AT364675B (en) 1976-04-23 1977-04-25 INSECTICIDE PREPARATION
CS772711A CS214851B2 (en) 1976-04-23 1977-04-25 Method of making the chiral acid ester
NZ183938A NZ183938A (en) 1976-04-23 1977-04-26 Preparation of a chiral acid ester of(s)- -cyano-3-phenoxybenzyl alcohol
AU24595/77A AU512155B2 (en) 1976-04-23 1977-04-26 Preparation of chiral acid esters of chiral alcohols of structure (s)
IL51958A IL51958A (en) 1976-04-23 1977-04-27 Process for inversion of configuration of chiral acid esters of alpha-cyano-3-phenoxybenzyl alcohol,chiral esters of(r)or(s)alpha-cyano benzyl alcohol with dimethyl-3(r)dihalovinyl-1(r)cyclopropane-carboxylic acid and insecticidal compositions containing them
FR7717014A FR2421876A1 (en) 1976-04-23 1977-06-03 Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod.
GT197957492A GT197957492A (en) 1976-04-23 1979-04-20 TRANSFORMATION PROCEDURE OF AN OPTICALLY ACTIVE ALPHA-CYAN SECONDARY ALCOHOL QUIRAL ACID ESTER OF ES TRUCTURE (K) INTO A QUINAL ALCOHOL ESTER OF SECONDARY ALCOHOL ...
AT125880A AT366028B (en) 1976-04-23 1980-03-06 METHOD FOR PRODUCING A (D) -ISOPROPYL-P -CHLORPHENYLACETIC ACID ESTER WITH THE (S) -ALPHA-CY-ANO-3-PHENOXYBENZYL ALCOHOL
CS81436A CS214852B2 (en) 1976-04-23 1981-01-21 Insecticide means
SE8204715A SE449359B (en) 1976-04-23 1982-08-16 (S) ALFA-CYAN-3-PHENOXYBENZYL-2,2-DIMETHYL-3R- (2,2-DICHLOROVINYL) -CYCLOPROPAN-1R-CARBOXYLATE AND ITS USE IN INSECTICIDING COMPOSITIONS
SG232/84A SG23284G (en) 1976-04-23 1984-03-12 Cyclopropane carboxylic acid esters
SG231/84A SG23184G (en) 1976-04-23 1984-03-12 Chiral acid esters
HK518/84A HK51884A (en) 1976-04-23 1984-06-22 Chiral acid esters
HK519/84A HK51984A (en) 1976-04-23 1984-06-22 Cyclopropane carboxylic acid esters
NLAANVRAGE8502001,A NL188676C (en) 1976-04-23 1985-07-11 PROCESS FOR PREPARING A PREPARATION WITH INSECTICIDE ACTION BASED ON AN ESTER OF A CHIRAL 2,2-DIMETHYL 3R- (2,2-DIHALOGENIC VINYL) -CYCLOPROPANIC-1-CARBONIC ACID WITH AN OPTICALLY ACTIVE ALPHA-CYANO-PHENOHENOXENE.
MY509/85A MY8500509A (en) 1976-04-23 1985-12-30 Cyclopropane carboxylic acid esters
DK317589A DK170732B1 (en) 1976-04-23 1989-06-27 Insecticide 2,2-dimethyl-3R- (2,2-dichlorovinyl) -cyclopropane-1R-carboxylic acid S-alpha-3-phenoxybenzyl ester and insecticide preparation
HRP-1047/77A HRP931394B1 (en) 1976-04-23 1993-11-11 Process for the transformation of esters, cis or trans-2,2-dimethyl-3r(2,2-dihalogeno vinyl)-cyclopropane-1r of carbixilic acid
MD94-0277A MD245C2 (en) 1976-04-23 1994-09-08 Method of preparation of ether of (S)-a-cyan-3-fenorybenzol cis-or trans-2,2 dimethyl-3R-(2,2)-dihalogenvenil cyclopropan-1R-carbonic acid

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FR2458542A1 (en) * 1979-06-12 1981-01-02 Roussel Uclaf PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE ALCOHOL A-CYANES
EP0022382A1 (en) * 1979-06-06 1981-01-14 FMC Corporation Crystalline insecticidal pyrethroid enantiomer pair, process for preparation and composition
FR2470117A1 (en) * 1979-11-27 1981-05-29 Shell Int Research ESTERS DERIVATIVES OF CYCLOPROPANECARBOXYLIC ACIDS, THEIR PREPARATION AND THEIR APPLICATION AS PESTICIDES
FR2470602A1 (en) * 1979-12-04 1981-06-12 Roussel Uclaf Acaricidal compsn. for control of animal ticks and mites - contains (s)-alpha-cyano 3-phenoxy-benzyl 1R, cis-2,2-di:methyl-3-2,2-di:chloro:vinyl-cyclopropane-1-carboxylate
FR2471187A1 (en) * 1979-12-10 1981-06-19 Roussel Uclaf NEW COMPOSITIONS FOR THE CONTROL OF PARASITES OF HOT-BLOOD ANIMALS
FR2481275A1 (en) * 1980-04-23 1981-10-30 Shell Int Research PROCESS FOR THE PREPARATION OF ESTERS DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACIDS
FR2481274A1 (en) * 1980-04-23 1981-10-30 Shell Int Research PROCESS FOR THE PREPARATION OF CYCLOPROPANE CARBOXYLIC ACID ESTER DERIVATIVES

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GB1599876A (en) * 1977-06-13 1981-10-07 Shell Int Research Conversion of a stereoisomer into its diastereoisomer
CH635563A5 (en) * 1977-07-07 1983-04-15 Sumitomo Chemical Co PROCESS FOR THE PREPARATION OF AN OPTICALLY ACTIVE ALPHA-CYANO-3-PHENOXYBENZYLE.
FR2402411A1 (en) * 1977-09-08 1979-04-06 Roussel Uclaf APPLICATION AS A PESTICIDE, IN THE FIGHT AGAINST MITES AND AGAINST NEMATODES PARASITES OF PLANTS, OF ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS WITH DIHALOVINYL CHAIN AND THE COMPOSITIONS OF ACARICIDES AND NEMATICIDES CONTAINING THEM
CA1215717A (en) * 1977-09-26 1986-12-23 Samuel B. Soloway Process for converting a stereoisomeric ester into its diastereoisomer
JPS54103831A (en) * 1978-01-27 1979-08-15 Sumitomo Chem Co Ltd Separation of stereoisomers of higher active cyanoo33 phenoxybenzyl 22*44chlorophenyl**isovalerate
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FR2419939A1 (en) * 1978-03-17 1979-10-12 Roussel Uclaf PROCESS FOR PREPARING AN OPTICALLY ACTIVE A-CYANE ALCOHOL ETHER
FR2428029A1 (en) * 1978-06-06 1980-01-04 Roussel Uclaf ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS SUBSTITUTED BY A-CYANE ALCOHOL, PROCESS FOR THEIR PREPARATION AND INSECTICIDE OR NEMATICIDE COMPOSITIONS CONTAINING THEM
JPS55104249A (en) * 1979-02-05 1980-08-09 Sumitomo Chem Co Ltd Optically active carboxylic ester its preparation, and insecticide, and acaricide comprising it
JPS55104253A (en) * 1979-02-06 1980-08-09 Sumitomo Chem Co Ltd Stereoisomer of more active carboxylic ester, method of obtaining it, insecticide and acaricide comprising it
US4308279A (en) * 1979-06-06 1981-12-29 Fmc Corporation Crystalline, insecticidal pyrethroid
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JPS56133253A (en) * 1980-03-24 1981-10-19 Sumitomo Chem Co Ltd Optical isomer of cyanohydrin ester, its production and insecticide and acaricide containing the same as effective ingredient
US4260633A (en) * 1980-04-21 1981-04-07 Zoecon Corporation Pesticidal esters of amino acids
JPS5793948A (en) * 1980-12-02 1982-06-11 Sumitomo Chem Co Ltd Preparation of stereoisomer mixture of higher active phenylacetic ester derivative
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HU198373B (en) * 1986-01-08 1989-10-30 Chinoin Gyogyszer Es Vegyeszet Artropodicide composition containing trans-cipermetrin isomeres and process for producing the active components
DE3522629A1 (en) * 1985-06-25 1987-01-08 Bayer Ag METHOD FOR PRODUCING SPECIFIC ENANTIOMER PAIRS OF PERMETHRINIC ACID (ALPHA) CYANO-3-PHENOXY-4-FLUOR-BENZYL ESTERS
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2447899A2 (en) * 1979-02-05 1980-08-29 Roussel Uclaf Insecticidal (S) alpha-cyano-3-phenoxy-benzyl alcohol ester(s) - are prepd. by esterification of the alcohol with 2,2-di:methyl-3-di:halo:vinyl-cyclopropane-1-carboxylic acid
EP0022382A1 (en) * 1979-06-06 1981-01-14 FMC Corporation Crystalline insecticidal pyrethroid enantiomer pair, process for preparation and composition
FR2458542A1 (en) * 1979-06-12 1981-01-02 Roussel Uclaf PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE ALCOHOL A-CYANES
EP0021925A1 (en) * 1979-06-12 1981-01-07 Roussel-Uclaf Process for preparing optically active alpha-cyanoalcohols
FR2470117A1 (en) * 1979-11-27 1981-05-29 Shell Int Research ESTERS DERIVATIVES OF CYCLOPROPANECARBOXYLIC ACIDS, THEIR PREPARATION AND THEIR APPLICATION AS PESTICIDES
FR2470602A1 (en) * 1979-12-04 1981-06-12 Roussel Uclaf Acaricidal compsn. for control of animal ticks and mites - contains (s)-alpha-cyano 3-phenoxy-benzyl 1R, cis-2,2-di:methyl-3-2,2-di:chloro:vinyl-cyclopropane-1-carboxylate
FR2471187A1 (en) * 1979-12-10 1981-06-19 Roussel Uclaf NEW COMPOSITIONS FOR THE CONTROL OF PARASITES OF HOT-BLOOD ANIMALS
FR2481275A1 (en) * 1980-04-23 1981-10-30 Shell Int Research PROCESS FOR THE PREPARATION OF ESTERS DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACIDS
FR2481274A1 (en) * 1980-04-23 1981-10-30 Shell Int Research PROCESS FOR THE PREPARATION OF CYCLOPROPANE CARBOXYLIC ACID ESTER DERIVATIVES

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PL117200B1 (en) 1981-07-31
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CS214851B2 (en) 1982-06-25
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GB1582595A (en) 1981-01-14
US4136195A (en) 1979-01-23
CA1130311A (en) 1982-08-24
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US4133826A (en) 1979-01-09
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SE449359B (en) 1987-04-27
GT197957492A (en) 1980-10-11
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ATA289677A (en) 1980-07-15
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SU990082A3 (en) 1983-01-15
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